Mad Men's Bob Benson: Good Guy, or Some Kind of Spy? View the Evidence and Make the Call

Whether Mad Men‘s Bob Benson is an earnest do-gooder or a nefarious weasel is as contentious a debate as whether to sell margarine based on cost or taste.

Though he’s been on the fringe of the action since his introduction in the Season 6 premiere, the new accounts guy (played by James Wolk) is all Mad fans want to talk about. (Well, him and the “Will Megan meet Sharon Tate’s fate?” question.)

Theories on Benson’s true identity – government spy? undercover reporter? Don’s illegitimate son? – abound. And while we’re not yet sure exactly why he’s turned up at Sterling Cooper Draper Pryce Cutler Gleason Chaough Or Whatever They’ll Eventually Call It, we’ve noticed that Benson is a keen observer at life within the firm.

TVLine has monitored the mysterious Mad man’s activities for the season to date, and the gallery below presents his whereabouts in each episode – along with what he appears to be saying/doing in the scene… and what we imagine he’s actually thinking.

We think we’ve caught the big stuff (and most of the small stuff), but the dude is cagey; if we missed any key Bob Benson moment, shout it out in the comments. And while you’re there, make sure to log your thoughts on the ad-agency newbie, as well as any alternate theories on what brings him to Madison Avenue in the late ’60s.

A lot of the strength found in the theories that Bob is some kind of plant or super villan seems to come from the fact he was phoney about whether his dad was dead or nursed back to perfect health.
Isn’t it possible he is just a proto-Smithers boot-licker of some kind?

Can’t we just have a nice, normal guy on this show for once. LOL Well maybe Ken fits that sometimes. I get how others want to think he’s up to something but I’m tied of all of that. Plus not everyone in this world is so cagey. Just wondering if we all are reading way too much into things. I like James Wolk from when he was on “Political Animals” and I know I’d hate it if Bob turns out to be up to something.

This! I really think people are reading too much into this (although with Weiner one never knows). I feel like Bob is basically the chum for these sharks, a contrast to show what people in a less fast-paced and competitive environment are like. As I said to my friend last weekend, “He’s the nice guy who gets eaten alive for doing nothing more than trying to be good to people.” I could be wrong, of course, but I think the theories about the character are a bit extreme compared to what the reality will be.

I think that his comments to Ken about his father dying and then telling Pete how his father has recently been nursed back to perfect health shows he’s not just the nice normal guy. At minimum he’s showing that he will say anything to get ahead whether it’s true or not. Normal on TV is boring. Bob is becoming interesting. And I hope we get to the gist of his being there soon – he’s starring in a new series in the fall with Robin Williams, so he may not be back next year.

Or, could both be true. At one point his father may have been nursed back to health. But he eventually died. It could also be true that he (A) is up to something even if it’s just trying to get in good and play the game AND (B) really does like Joan. Having said that, Mad Men is like Shakespeare: nothing is an accident/incidental.

Both can’t be true. Six months ago (in Mad Men time) Bob’s father was dead. Last week he made it clear that the only reason the nurse was available now was that his father was all better – Do you really think a nurse will wait around for over six months to find work? No, Bob’s up to something. I hope his interest in Joan is real, though. She needs a break in the romance department, and he’s hot.

Bob is disingenuous. Everything he says and does he says and does because he believes it will help him succeed in business. He lied about his father. That’s all. It was a lie of convenience, to help ingratiate himself in the moment. He may actually be a nice, if naive, guy. He’s a believer and a joiner. Right now he has youth, good looks and a sense of white entitlement. He’s not a horrible person but he does have faith in the “natural” order of things. He serves as a contrast to the upheaval in society…playing right outside their doors, down on the street. America belongs to him, so he’s told, if he works hard and follows the rules. But that’s all changing.

True but he can be both and if he is up to something that makes it more exciting! No? It’s not exactly like when Lane was up to something last season and they showed him doing it midway through the season to see it pan out in the end. I have another theory on the spy thing…. Maybe he is investigating Dick Wittman! :)

Nothing could convince me that he’s NOT Don’s illegitimate son. He comments on how much Don knows about Pennsylvania – if teenage Don had a child with Aimee the ‘lady of the night,’ it would have been in Pennsylvania, where he grew up in that whorehouse. He has several stories about his father, which causes none of them to seem honest. Maybe because his real father is Don?? That makes sense to me. I can’t wait to find out if I’m right!

I’m with you on this one. He looks like Don, he has the same talent at reading people, and, as is Don, he is a good liar. Genetics are not to be underestimated. What could Bob (same name as Don’s son with Betty) have in mind…we shall see.

No-not real Don Draper’s son unless real Don Draper got another woman pregnant other than Anna real Don’s wife, whom Dick/Don befriended and took care of-the blond with the bad leg who lived in CA. Could be Dick/Don’s prostitute’s son and Dick/Don’s son and somehow through Dick/Don’s half-brother (who somehow found Dick/Don years ago in the newspaper) or by other means, he found Dick. Benson could have his mom’s last name or his adoptive dad’s name. Or use a fake last name. But I do believe he’s up to something. One minute his dad’s dead; the next a good male nurse has nursed him back to health. And for some reason last week Joan said to Bob that Pete wouldn’t ask Bob for help because he’s too proud. I would think Pete wouldn’t ask Bob because Bob’s not in his radar. But Joan seems to know something we don’t.

I think he’s a weasely ladder-climber who tries to ingratiate himself and get a lot of dirt to gain power. Or perhaps he is Matt Weiner’s version of J. Pierpont Finch, in which case they are building to a major smack down scene with Bert Cooper schooling him and firing him in the ultimate oh wow moment: the real Finch taking down the wannabe.

Awesome theory! I really think he’s Don Part 2, not his son, just the new generation of ambitious, handsome, smooth ladder climber. J. Pierrepont Finch works, too, though, especially with Burt/Ponty himself in the office.

What has always seemed odd to me is that Benson says he’s “in Accounts, upstairs.” But as Roger Sterling asked him last Sunday, “Why are you always down here? Go back upstairs where you belong!” There’s one scene last Sunday with Bob answering “his” phone – but the desk and surrounding area looks to be terribly generic. Are we *sure* he works upstairs in Accounts? Are we *sure* he even works there at all? What if he’s borrowed a page from “How to Succeed” and is working for “a company that is so large no one know exactly what the other person is doing.” Maybe Bob Benson is really a window-washer who, like Finch wanted to be on the inside.

I have no idea where they’re taking this with Bob, but I kind of learn toward your theory that he’s just an extremely ambitious ladder-climber. I’m waiting for him to get someone fired so that he can move up in the company or else get some prime dirt on a partner that gets him promoted.

First, can’t stand this guy. No matter the role he can’t wipe that constant smirk off his face and it ruins his characters. Be serious for once. Second, I guess his character is a cop or some sort of investigator looking into the company after what Lane did and his ultimate suicide. He seems to be buttering people up for info and has no real job other than that and handing out coffee.

I almost wrote spying for another ad agency. People might want to know how Don does what he does. The IRS is good, or even some other Fed. Sometimes even I forget Don Draper is a fake identity after all.

If he’s there to steal secrets, they should have sent in a creative, not a salesman. The creatives meet and work with Don. The sales guys work with Pete. I think this may be more about Pete than Don. Although being Don’s son is an intriguing idea.

I think he may be a g-man, sent to uncover the real identity of don draper. Remember, don/dick made a fortune in the sale of SC during season 2, which would motivate the IRS. Bob could be acting very kindly to Pete for 2 reasons. First, Pete knows that don is really Dick Whitman, and Pete has a friend, Russ (?) at the DOD. Perhaps Russ is the one who sent Bob, and Bob knows he needs to get close to Pete.

Bob does not work at the agency. There is no way anyone in advertising would ever hire anyone like him in any department. He is just too normal, plain, boring. Especially in an agency like Sterling Cooper. No one would ever say they work “in accounts.” Mad Men usually gets it right, so this seems to be an intentional “error” rather than a writer’s oversight in ad terms. There is “account service” and ” accounting” but not “accounts.” He has no role. The dude is not really employed there. He has somehow managed to float in as a pretender, and for some reason Joan may know and be keeping the secret. Don’s son? That’s way to easy. I doubt it. I find him highly annoying and he doesn’t fit in the show, just like he doesn’t fit in the agency! So there has to be a reason. But what?

Bob does work there. Didn’t Joan save his job right when they were going to ax him? He had just taken her to the hospital and performed his sweet talking magic and Joan saves his job. How would he be in the fire list if he didn’t work there?

Agree there is something up with him but believe the Don using coffee for Cooper to get his job connection is right on. His lying and sucking up seem to just point to the same qualities in Don’s and his ability to say or do anything necessary to get what he wants.

Likely there is more to the story but an unknown son? Seems to soap opera-Ish for Weiner. Couldn’t he be the younger Don without having to actually be related to make the point?

As much as I am enjoying the commentary on Bob and love James Wolk, what does this say about the season if THIS is the most interesting thing to talk about? No real chatter on the Don/Peggy/Ted triangle. Don is being an ass, again. Roger is feeling sorry for himself, again. Peter can’t figure out why people won’t respect him, again. If it wasn’t for Bob or dare I say Megan, Mad Men wouldn’t have much to talk about.

Megan’s never been interesting to me. She’s a tantrum-throwing, selfish child who married the wrong man. And she gets hit on a lot by her show-within-a-show co star. With Megan what you see is what you get. Meh. Bob has a secret and a strategy. And he’s cute as hell.

Regarding your comments about Megan. You took the words right out of mouth. Honestly, I just can’t stand her – character and she is certainly is not a trophy wife. Obviously this marriage was doomed from the start and kept getting more bizarre with every episode. Remember the Howard Johnson trip? I still don’t know where she went … Then the birthday gift ( that embarrassing song she sang to Don). Ugh. I say goodbye Megan and get set for another divorce – don will go broke.

I think his turning out to be Don’s son is a typical soap opera cliche which this show is but at a higher level. Just as I’d love for Megan to run off with Harry Hamlin. Also, not to be nit-picky, but what happened to all of Betty’s loose skin from losing a ton of weight? If only it were that easy. My fave touch in the series was Sally reading Rosemary’s baby. Classic.

It might be too soapy an idea but isn’t there a soap-within-a-show right now on Mad Men with To Have And To Hold? A revelation such as Bob’s being Don’s long-lost son would serve as a highly ironic counterpoint to that.

They would do that quite often, and brilliantly on Twin Peaks with a fictional soap-within-the-show called ” Invitation to Love” that would often mirror the soapy plot devices in Twin Peaks (like the deceased Laura Palmer (Sheryl Lee)’s cousin with an uncanny resemblance, Maddy (Sheryl Lee).

This season “Mad Men” is just not progressing…..I lived in the 60s, worked for an ad agency in L.A. These were some of the most exciting times in our history, and the series needs to be affected more by the changes in our society, and focus less on Don alone.

Thank you, Nancy! My thoughts exactly! Even though I was around Sally Drapers age in the 60’s that era had permeated every aspect of life, They nailed the cultural impact in the first season. After that it might as well be 1999.

Or not. I don’t think he is as important as you keep trying to point out. A lot of people lie about the dumbest things. If it fits the moment, they just make up something to add to the conversation or make themselves look good. If he is an agent of some sort, I will be impressed by the guesses here.

He obviously tries to kiss butt all the time and he has lied to both Ken and Pete about things to try and justify his actions. First his dad is dead and he would appreciate any gesture then his father has been nursed back to health by the “well-bred” male nurse. Notice it is a male nurse. How many of those were there in 1968? Could it be a colleague in whatever he is in bed with? Even gay men would love to get a gander at Joan’s amazing assets.

Who knows, with Weiner holding all his cards so close to the vest. No one knows the guy, so apparently no one hired him. I wouldn’t be surprised to see Joan be the one to break the case by simply checking to see if Bob has ever even drawn a paycheck.

Maybe Bob is a paralell to an earlier version of Don, rather than his illegitimate son. In an earlier season, there’s a flashback to when Don was first hired by Roger. Don has the same countenance as Bob Bensen for those flashbacks . The ironic thing is that Roger is unsure when Don shows up for his first day of work whether he actually hired Don. It is slightly inferred that Don just started showing up and he got himself the job by being around (okay this might be a slight exaggeration). Do we ever really see Bob do any work? Bob, at least to me, is appearing as if he is hanging around, getting to know people and will maybe replace Don in a symbolic sense. It would kind of go along with this theme of Don being disconnected from the current, free, younger generation( i.e. Meg’s generation, Peggy’s generation, Ginsberg’s(if I spelled that wrong please feel free to correct) generation,etc.).

My theory is that he is an undercover journalist, investigating the advertising world in the ’60s. Simply because he ‘just shows up’ and seems to fit in, no one questions him, he doesn’t seem to report to anyone. What is going to come out of his time at the agency is a ‘best seller’ on advertising or an investigative piece for the NY Times, WSJ or some major newspaper. After all this is also the era of Woodward and Bernstein.

I can’t say I really believe this, but it has crossed my mind that Bob might be a dangerous guy. All the speculation about Megan/Sharon Tate made me think of serial killers like Manson and Ted Bundy, the former of whom was considered attractive and fairly successful (and is speculated to have begun killing around 1968/9). I really have nothing here, except that Bob seemingly lied about his father and the fact that murder, or at least more violence, is being foreshadowed pretty heavily. So maybe the mystery surrounding Bob and the Tate references are not unrelated.

There’s a scene in ep9, “The Better Half”, where Don and Betty visit Bobby at camp and Bobby, played by Mason Cotton Vale, says he’s Bobby 5, which is almost true because three other boys have played Don’s son, Bobby before him. Then he says, Bobby 1 left. That could mean Bobby 1 is Don’s first son, who we haven’t seen yet. Bob Benson? Or maybe it could mean Megan’s aborted son.

On the other hand, Bob Benson is always holding and handing out those coffee cups, as someone here pointed out. They could be bugged for an FBI investigation.

And who knows, both theories could be related. Or both a red herring. Anyway. It’s a good show.

Bugged paper coffee cups in the 1960s? LOL! Bugs back then were huge, so you’d see them easily. Plus they aren’t waterproof so if you try hide them in the coffee they would short out and be seen as people drink. Funny idea though.

Mad Men fans have at least enough time to be Mad Men fans, a show that’s full of subtle under tones. I wouldn’t count it’s fandom and the small devotion of time on all it’s various moving parts and pieces as a detriment or even a waste. It’s playful speculation, nothing more.

I just think he’s trying to get a job. However I bet that it turns out that he’s not that nice of a guy and I betting he turns out to be so backstabbing and conniving that he puts Pete Campbell from Season’s 1 and 2 to shame. I bet Joan falls for him and he ends up using her to get himself a nice, secure and coushy job at the firm.

Sometimes I wonder if them not allowing Joan to have a ‘good man’ is a kind of punishment for her being so beautiful and the object of every mans fantasy. Most women on the show admire Joan & wish they were her but they don’t see that everything she has or had either didn’t work out I.e. her marriage to Kevin…or she had to do vile things to get it..like sleeping w/the Jaguar guy to make partner. I’d love to see her with someone who will truly love her…I’m secretly still hoping for Roger & Joan to get back together & go public with it. Hey I can dream right? ;)

Bob is all style and no substance. He’s completely aware of his image to others as a
charming, helpful and clean-cut guy, and he uses it. But there’s nobody home. In tonight’s
episode (“Tale of Two Cities”) he’s not at all pleased that Jim has thrown him into the lion’s cage with the Manischewitz account. He’s actually in a panic – though he hides it — when he learns that Michael is trying to get out of the meeting and uses his Dale Carnegie technique to successfully talk Ginzburg back into going. But his abilities as an account exec are exposed when he comes back with the news that the meeting was a bust and the firm will lose Manischewitz. However he’s already managed to win over Jim — not too birght himself — who wishes to pack the office with “his” people. He’s an extremely dangerous member of the that office and will probably wreak havoc before he’s finally found out.

Maybe Bob is a sociopath… perhaps even a serial killer. Nice guy, studies people while being somewhat unassuming. This season they talk a lot about the various grizzly killings that were happening in that era, the “Nurses” are brought up quit a bit. The odd crimes going on, like the lady who broke into Don’s apartment. Maybe Bob is the one that kills Megan, combining both show rumors in one arc.

Not a truly nice guy,(though it would have been nice for Joan), because a truly nice guy wouldn’t have offered to pay for Pete’s hooker/lied about his dad’s death; and a nice guy would have friends/places to go other than work. He’s like a younger version of Don, a sociopath. I think at the end he’ll either lead to the firm or Don’s downfall, or be extremely violent in some way as others have suggested. AAAH! Speculating is my favorite part of watching the show!

Anyone remember when Bob was first introduced? Wasn’t in an elevator and Don had no idea who he was? Have we even seen Bob working on anything in accounts? The only time we see him is when he’s just randomly moseying around the creative department.

Isn’t there a chance that Bob doesn’t even work at the agency, and he’s just been pretending to work there, and everyone in the company is just too busy (or drunk) to realize he’s not even part of the company? This makes me think he’s some sort of spy, and he’s just gotten really lucky to have gotten so far.

I think he represents the new school. He doesn’t drink but offers to buy them, most likely graduated college but isn’t going to just jump in the dirtiness which is advertising, he remains ignorant of all past wrongs and attempts to stay clear away from new ones being committed. He is the change of generation from don, roger, and Pete.

How come no one’s mentioned the fact that Bob Benson had to psych himself up before a meeting with a motivational record? That’s got to infer some sort of mental instability right? As confident as he appears, he’s really not that person naturally.

Judging from the season 6 poster (a sketch featuring 2 Dons, or 2 halves of the same person) and all that has transpired in S6, this season has been about all the faces of Don or even the archetypes that make up his character. I think many characters are meant to represent these pieces of Don. In Peggy we see the professional dynamo side, in Pete we see the adulterer/home wrecker, plus think about Betty, Megan, and Sylvia all representing certain female archtypes that reflect what he wants and/or needs. I think it’s also notable that 2 agencies joined together and that there is friction between Don and Ted, who are basically the same person for each agency (reflections, have you). I have a suspicion that Bob plays a part in this – perhaps the future Don? I think the “5 Bobbys” mentioned by little Bobby at camp is also a notable hint. Mad Men is full of subtle meanings or signs/symbolism, sometimes they mean something, sometimes then don’t…why I love this show!

Dang. All interesting theories. Weiner has misled his audience before (Peggy’s son, as her nephew, maybe). With Megan in a soap opera, I wouldn’t be surprised if MW pulls a big reveal at the end. Trying not to over analyze too much …. it has been fun to speculate BB’s motives all season!

It’s really simple
Bob is a private detective hired by the Widow of Layne Pryce to dig up dirt and ruin the people she feels murdered her husband. She’s paying him the 10,000 that the firm gave her.
He’s sucking up to Pete because Pete and Don clash often and loudly in the office. Knowing that Pete will eventually blow his top and lose control of his mouth Bob is just pushing for the big reveal.
He’s going to find out Don isn’t Don
He’s also cultivating Joan because she is the partner closest to the books and if the Widow were planning a raid or lawsuit she would want to know the assets of the firm. Also she might want info on exactly how Joan became a partner which was in a technical sense illegal ( IE Prostitution) which might also be used in court or in getting people arrested.

I think if you have worked in a big agency, like I have you realize. He is just a kiss up who wants to make his way up the food chain. There are so many people like that in large agencies, it ridiculous. He is going to end up being Joans new man, and her Pete and Bob will start makin’ moves.

He’s CIA; the agency planted people in ad agencies all the time. And this is a time of all sorts of stuff going on the the U.S. Gov’t. Bob may be scoping them out to find out whether they are trustworthy enough to handle gov’t business and needs to know what everyone’s Achilles Heel is because that could compromise them.

Last episode when Cutler was arguing with Ginsberg, he yelled at Benson when he interjected himself into the conversation asking “Why are you always down here!? Get back to work!” because as an accounts man he should be upstairs not in creative….so yes why is he always down there, just floating around, never seeming to be working….the photo posted in this article of when he set up shop on the random table…I never thought about that but I definitely think it’s because he doesn’t have a real work space. Spy, Fed, or whatever…he is up to something. Honestly if he isn’t…how utterly boring.

From a practical standpoint (as others have hinted in the comments) shows like this are always in danger of getting “too dark.” So it does help to have a (seemingly) nice guy around, when everyone else is jealous or provoked.
Then again, you have to acknowledge some of the characters have a “symbolic” identity, in addition to their “face value.” To me, a character that descends a staircase from up above the show’s office set (into the “real world” of the show, from a realm we’ve never seen), announcing himself as being “upstairs in accounts,” is symbolic of some Heavenly angel of Judgment Day– which will also feed into the teasing speculation that he could “snap at any moment.”
But, to me, that explains why he’s so insistent about finding out and getting involved and observing. And his seemingly stunned reaction this past Sunday, when the Jewish ad guy says, “tell me the truth– are you a homo?” I almost don’t think Bob has a sexual identity (yet). This may change, he may become more of a regular character, but initially, he does seem almost impossibly angelic.

I don’t think the IRS or the FBI would have the remotest possible interest in Sterling Cooper. What has anyone done wrong there? And I doubt a journalist would go undercover for months there. What investigation would warrant that big an expenditure (i.e. a salaried journalist not producing any other copy for months) and why would an ad agency be the target for that skullduggery? I don’t think Benson is Don’s illegitimate son via the hooker. Don is early 40s – the zoobie zoobie zoo episode was his 40th birthday party, I think, and in calendar time it’s a year or two previously – and Benson is old enough to make it barely mathematically possible. But also, he seems pretty well-bred, a lot more likely to have been the son of people with BBH for three generations than the out of wedlock son of a small-town hooker. It is interesting, though, that there’s been so little explanation of what he does there, who hired him, where he came from. Should we conclude he’s now banging Joan, lucky devil? I was unclear form the context where she and he were headed for an overnight, bang-positive trip to the beach sans kids – or a day trip, maybe with the baby in tow, and he does already have his swimsuit on, less likely to be bang-positive. I don’t see Joan as being interested in someone just out of college, Benson is probably a little older than that.

If Joan is the office manager/partner in the firm, then I think she would know who he is and what his job is, don’t you think? That doesn’t mean he didn’t lie to get in there. Don’s son, corporate spy, government spy, or just a regular weasel? Also, I wonder why the heck he always gets outside coffee when they already have coffee in the office kitchen. And he’s always walking around with it. Whatever, he’s too weird for me even if he is good looking.

So, what is behind Bob Benson’s facial expressions will tell it all. Here are the keys. THE SINCERE SMILE- As pleasant as a clergyman, which he was before he dropped out of priesthood. Still altruistic, but horny. KIND TO EVERYONE – because he has 18 months to live. And in a future plot twist, modern medicine finds the cure after Joan agrees to fulfill his dream of leaving a child behind when he “dies”. Joan stabs him with a hot poker when he survives. QUIET CONFIDENCE – because he is secretly Bert Cooper’s love toy, and is the sole beneficiary of the old man’s will, which makes him a full partner when Bert chokes to death on ancient wine salvaged from the wreck of a pre-Christian Etruscan trader at the bottom of the Med. Bob is kind, nice, and confident that he is going to be the boss of all these people someday.

I think if he’s up to something sinister, it has to do with either the money or info that Joan has access to, or Pete. If you look at how the agency evolved, in the beginning, Sterling Cooper was mostly WASPs. Now they’re all gone from Don’s team, but they still control the accounts department — those ‘elite’ family / social / school connections were necessary to bring in and maintain business, but now that’s changing. Ken doesn’t want to use his family connections, being a WASP isn’t helping Roger any more (look at how he was dressed when he got punched in the balls by hippie Danny!), and Pete’s family is now his biggest liability. Plus Joan just proved that someone of a lower social class can get a meeting with a Fortune 500 company. Bob’s secret might just be that he’s a merciless social climber, like a young Great Gatsby.

The fact that Bob was listening to a how-to-succeed-in-business record and later, when Ginsberg was having a panic attack, regurgitated the same sort of motivational-speak to help him through it makes me think Bob is just a naive, optimistic, mid 20th-century white guy trying to lasso the American Dream. 35 years from now he’ll lose his job, his pension, his savings and his house. All because he did what he was supposed to do.

Bob’s a comer at the outset of his career. Anyone remember how Don Draper got his start at Sterling Cooper? Bob’s the account-side equivalent; bold ambition tempered perhaps by the nice guy persona. The nice guy part makes him more like the anti-Pete Campbell.

Agree. Bon mirrors Don’a behavior but he seems to be less conflicted and therefore has less vices. Kind of like many in today’s society. Same immoral or amoral conduct today as our elders but with less of a conscious or guilt and so less.

Greed is good was not solely an eighties phenomenon. Weiner may be simply making larger points about society.

Bob seems to be the only one who is not affected by the external world’s undoing. He haut floats along holding his two coffee cups and a strange grin on his face.